JPS60248692A - アセチルリン酸塩を製造する方法 - Google Patents

アセチルリン酸塩を製造する方法

Info

Publication number: JPS60248692A
Authority: JP; Japan
Prior art keywords: acetic anhydride; phosphoric acid; molar ratio; lithium; acid
Prior art date: 1984-05-25
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

JP10591484A

Other languages

English (en)

Japanese (ja)

Other versions

JPH049796B2 (cs

Inventor

Yoichiro Ueda

陽一郎上田

Teruo Otomo

大友　輝雄

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Daicel Corp

Original Assignee

Daicel Chemical Industries Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1984-05-25

Filing date

1984-05-25

Publication date

1985-12-09

1984-05-25 Application filed by Daicel Chemical Industries Ltd filed Critical Daicel Chemical Industries Ltd

1984-05-25 Priority to JP10591484A priority Critical patent/JPS60248692A/ja

1985-01-16 Priority to DE8585100392T priority patent/DE3569530D1/de

1985-01-16 Priority to EP19850100392 priority patent/EP0153571B1/en

1985-01-22 Priority to US06/693,657 priority patent/US4753757A/en

1985-12-09 Publication of JPS60248692A publication Critical patent/JPS60248692A/ja

1992-02-21 Publication of JPH049796B2 publication Critical patent/JPH049796B2/ja

Status Granted legal-status Critical Current

Links

LIPOUNRJVLNBCD-UHFFFAOYSA-N acetyl dihydrogen phosphate Chemical class CC(=O)OP(O)(O)=O LIPOUNRJVLNBCD-UHFFFAOYSA-N 0.000 title claims description 40
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 107
239000012442 inert solvent Substances 0.000 claims abstract description 15
239000011541 reaction mixture Substances 0.000 claims abstract description 14
HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims abstract description 10
229910001416 lithium ion Inorganic materials 0.000 claims abstract description 10
239000007787 solid Substances 0.000 claims abstract description 9
230000000397 acetylating effect Effects 0.000 claims abstract description 4
229910003002 lithium salt Inorganic materials 0.000 claims description 11
159000000002 lithium salts Chemical class 0.000 claims description 11
238000004519 manufacturing process Methods 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
230000001376 precipitating effect Effects 0.000 claims description 3
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract description 78
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 63
235000011007 phosphoric acid Nutrition 0.000 abstract description 38
229910000147 aluminium phosphate Inorganic materials 0.000 abstract description 30
239000002244 precipitate Substances 0.000 abstract description 12
XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 abstract description 8
229910052808 lithium carbonate Inorganic materials 0.000 abstract description 8
150000003839 salts Chemical class 0.000 abstract description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
150000002642 lithium compounds Chemical class 0.000 abstract description 4
239000000758 substrate Substances 0.000 abstract description 3
108091000080 Phosphotransferase Proteins 0.000 abstract 1
238000013019 agitation Methods 0.000 abstract 1
102000020233 phosphotransferase Human genes 0.000 abstract 1
238000003756 stirring Methods 0.000 description 21
238000006640 acetylation reaction Methods 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 15
238000000034 method Methods 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
238000004811 liquid chromatography Methods 0.000 description 11
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 8
238000000926 separation method Methods 0.000 description 7
XLLNINGEDIOQGQ-UHFFFAOYSA-N [acetyloxy(hydroxy)phosphoryl] acetate Chemical class CC(=O)OP(O)(=O)OC(C)=O XLLNINGEDIOQGQ-UHFFFAOYSA-N 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
238000001556 precipitation Methods 0.000 description 4
238000007086 side reaction Methods 0.000 description 4
239000002002 slurry Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
229910019142 PO4 Inorganic materials 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
239000012345 acetylating agent Substances 0.000 description 3
230000021736 acetylation Effects 0.000 description 3
238000006911 enzymatic reaction Methods 0.000 description 3
239000011521 glass Substances 0.000 description 3
XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 3
238000002156 mixing Methods 0.000 description 3
235000021317 phosphate Nutrition 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 2
108010092060 Acetate kinase Proteins 0.000 description 2
ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
229910011197 Li2Co Inorganic materials 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
IZASLLIUFQPKOG-UHFFFAOYSA-N diazanium;acetyl phosphate Chemical compound [NH4+].[NH4+].CC(=O)OP([O-])([O-])=O IZASLLIUFQPKOG-UHFFFAOYSA-N 0.000 description 2
SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 2
-1 dilithium salts Chemical class 0.000 description 2
GOBPXJGOJYUOAF-UHFFFAOYSA-L dilithium;acetyl phosphate Chemical compound [Li+].[Li+].CC(=O)OP([O-])([O-])=O GOBPXJGOJYUOAF-UHFFFAOYSA-L 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000007824 enzymatic assay Methods 0.000 description 2
238000001952 enzyme assay Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
239000002994 raw material Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
102000001253 Protein Kinase Human genes 0.000 description 1
239000005456 alcohol based solvent Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000006389 diacetylation reaction Methods 0.000 description 1
150000004683 dihydrates Chemical class 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
150000002168 ethanoic acid esters Chemical class 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
ZUVCYFMOHFTGDM-UHFFFAOYSA-N hexadecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCOP(O)(O)=O ZUVCYFMOHFTGDM-UHFFFAOYSA-N 0.000 description 1
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
229940011051 isopropyl acetate Drugs 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
OBTSLRFPKIKXSZ-UHFFFAOYSA-N lithium potassium Chemical class [Li].[K] OBTSLRFPKIKXSZ-UHFFFAOYSA-N 0.000 description 1
RLQMPLKXFIXRCV-UHFFFAOYSA-L lithium;potassium;acetyl phosphate Chemical compound [Li+].[K+].CC(=O)OP([O-])([O-])=O RLQMPLKXFIXRCV-UHFFFAOYSA-L 0.000 description 1
239000002609 medium Substances 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1

JP10591484A 1984-02-01 1984-05-25 アセチルリン酸塩を製造する方法 Granted JPS60248692A (ja)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
JP10591484A JPS60248692A (ja)	1984-05-25	1984-05-25	アセチルリン酸塩を製造する方法
DE8585100392T DE3569530D1 (en)	1984-02-01	1985-01-16	Process for preparing solid acetyl phosphate salt
EP19850100392 EP0153571B1 (en)	1984-02-01	1985-01-16	Process for preparing solid acetyl phosphate salt
US06/693,657 US4753757A (en)	1984-02-13	1985-01-22	Process for preparing solid acetyl phosphate salt

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP10591484A JPS60248692A (ja)	1984-05-25	1984-05-25	アセチルリン酸塩を製造する方法

Publications (2)

Publication Number	Publication Date
JPS60248692A true JPS60248692A (ja)	1985-12-09
JPH049796B2 JPH049796B2 (cs)	1992-02-21

Family

ID=14420128

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP10591484A Granted JPS60248692A (ja)	1984-02-01	1984-05-25	アセチルリン酸塩を製造する方法

Country Status (1)

Country	Link
JP (1)	JPS60248692A (cs)

1984
- 1984-05-25 JP JP10591484A patent/JPS60248692A/ja active Granted

Also Published As

Publication number	Publication date
JPH049796B2 (cs)	1992-02-21

Publication	Publication Date	Title
Ballou et al.	1956	The synthesis and properties of hydroxypyruvic acid phosphate
Armarego et al.	1976	A highly stereospecific synthesis of (R)-and (S)-[2-2 H 1] glycine
JPH0841082A (ja)	1996-02-13	燐酸化試薬組成物、モノアルキル燐酸エステルの製造法並びにそれにより製造された組成物
Dolling et al.	1978	Synthesis and resolution of 3-fluoro-D, L-alanine-2-d: a selective deuteration via reductive amination with sodium borodeuteride
US5047223A (en)	1991-09-10	Separation of phosphoric acid from aqueous solutions of thiamine phosphates
Li et al.	2019	Synthesis of a non-natural glucose-2-phosphate ester able to dupe the acc system of Agrobacterium fabrum
JP3081016B2 (ja)	2000-08-28	結晶性チオニコチンアミド−アデニンジヌクレオチド燐酸カリウム塩及びその製造法
Salo et al.	1970	Synthesis of 2-acetamido-2-deoxy-α-D-mannopyranosyl phosphate and uridine 5'-(2-acetamido-2-deoxy-α-D-mannopyranosyl dipotassium pyrophosphate
US4154759A (en)	1979-05-15	Preparation of N-(phosphonoacetyl)-L-aspartic acid
US4659671A (en)	1987-04-21	Enzymatic separation of racemic mixtures of hydroxy compounds
JPH049796B2 (cs)	1992-02-21
SU580824A3 (ru)	1977-11-15	Способ получени фосфата кали
US4179464A (en)	1979-12-18	Preparation of N-(phosphonoacetyl)-L-aspartic acid
US5728359A (en)	1998-03-17	Method for the preparation of sodium ammonium phosphate
US4178306A (en)	1979-12-11	Preparation of N-(phosphonoacetyl)-L-aspartic acid
CA2012928C (en)	2000-06-27	Separation of phosphoric acid from aqueous solutions of thiamine phosphates
JPH048431B2 (cs)	1992-02-17
EP0153571B1 (en)	1989-04-19	Process for preparing solid acetyl phosphate salt
SU1594179A1 (ru)	1990-09-23	Способ получени тиаминтрифосфата
JPH0436158B2 (cs)	1992-06-15
SU983042A1 (ru)	1982-12-23	Способ получени кислых триполифосфатов кали
RU1775405C (ru)	1992-11-15	Способ получени 2 @ -дезоксинуклеозид-5 @ -0-(1-тио)трифосфатов
Mendicino et al.	1982	[19] Isomers of α-d-apiofuranosyl 1-phosphate and α-d-apiose 1, 2-cyclic phosphate
JPS59108799A (ja)	1984-06-23	新規なｓ−アデノシル−ｌ−メチオニン塩の製造法
US5340557A (en)	1994-08-23	32 P thiophosphate preparation